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Total Synthesis of the Potent Antitumor Macrolides Pladienolide B and D
Author(s) -
Kanada Regina M.,
Itoh Daisuke,
Nagai Mitsuo,
Niijima Jun,
Asai Naoki,
Mizui Yoshiharu,
Abe Shinya,
Kotake Yoshihiko
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604997
Subject(s) - moiety , metathesis , stereochemistry , ring closing metathesis , chemistry , total synthesis , salt metathesis reaction , ring (chemistry) , mechanism (biology) , computer science , combinatorial chemistry , philosophy , organic chemistry , epistemology , polymerization , polymer
Getting cross : The total syntheses of two pladienolides (see picture), which have prominent antitumor activity based on a unique mechanism of action, have been accomplished, and their absolute configurations were verified. The 12‐membered aliphatic macrolide structure was formed by ring‐closing metathesis, and the side‐chain moiety was coupled to the macrolide by Julia–Kocienski olefination or cross‐metathesis.

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